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Published TCIMAIL newest issue No.197
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Benzyne Precursors
No.134(October 2007)
- T2089
- 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate (1)
- M1882
- 4-Methyl-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate (2)
- M1883
- 2-Methyl-6-(trimethylsilyl)phenyl Trifluoromethanesulfonate (3)
- M1884
- 3-Methoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate (4)
- M1885
- 4-Methoxy-2-(trimethylsilyl)phenyl Trifluoromethanesulfonate (5)
- T2465
- 1-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate (6)
- T2466
- 3-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate (7)
- B3047
- 3,3'-Bis(trimethylsilyl)biphenyl-4,4'-diyl Bis(trifluoromethanesulfonate) (8)
- T2467
- 1,3,5-Tris[4-(trifluoromethanesulfonyloxy)-3-(trimethylsilyl)phenyl]benzene (9)
In general, generation of benzyne requires the addition of strong base or high temperature. However, benzyne precursors that can be used in a milder condition have been developed. 2-TMS-phenyl triflate (1) and its analogs are some of the excellent benzyne precursors, and react with fluoride ion to produce benzyne under mild conditions. Moreover, since these precursors don't generate iodobenzene which derives from the elimination group of iodonium-type benzyne precursors, it is possible to use it for the palladium catalyzed reaction. Therefore, these precursors are being applied to the efficient syntheses of polyaromatic compounds.
References
- 1)Y. Himeshima, T. Sonoda, H. Kobayashi, Chem. Lett. 1983, 12, 1211.
- 2)T. T. Jayanth, M. Jeganmohan, C.-H. Cheng, J. Org. Chem. 2004, 69, 8445.
- 3)A. Cobas, E. Guitián, L. Castedo, J. Org. Chem. 1997, 62, 4896.
- 4)D. Peña, S. Escudero, D. Pérez, E. Guitián, L. Castedo, Angew. Chem. Int. Ed. 1998, 37, 2659.
- 5)D. Peña, D. Pérez, E. Guitián, L. Castedo, J. Am. Chem. Soc. 1999, 121, 5827.
- 6)D. Peña, D. Pérez, E. Guitián, L. Castedo, J. Org. Chem. 2000, 65, 6944.
- 7)E. Yoshikawa, K. V. Radhakrishnan, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 7280.
- 8)Z. Liu, R. C. Larock, J. Org. Chem. 2006, 71, 3198.
- 9)U. K. Tambar, B. M. Stoltz, J. Am. Chem. Soc. 2005, 127, 5340.
- 10)J. Zhao, R. C. Larock, Org. Lett., 2005, 7, 4273.
- 11)TCIMAIL 2006, number 129, 16.
Related Compounds
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